Methanol → 3-Amino-6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione

HRID 1670505Notes

Reaction equation

HRID 1670505 reaction equation
C[Si](I)(C)C.[Cl:6][C:7]1[CH:50]=[CH:49][C:10]([CH2:11][CH:12]2[N:17]3[C:18](=[O:44])[CH:19]([NH:33]C(=O)OCC4C=CC=CC=4)[CH2:20][N:21]([S:22]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=4[Cl:32])(=[O:24])=[O:23])[CH:16]3[CH2:15][N:14]([CH:45]([CH3:47])[CH3:46])[C:13]2=[O:48])=[CH:9][CH:8]=1.CO>CC#N>[NH2:33][CH:19]1[C:18](=[O:44])[N:17]2[CH:12]([CH2:11][C:10]3[CH:49]=[CH:50][C:7]([Cl:6])=[CH:8][CH:9]=3)[C:13](=[O:48])[N:14]([CH:45]([CH3:46])[CH3:47])[CH2:15][CH:16]2[N:21]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])(=[O:24])=[O:23])[CH2:20]1

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 86761388Benzyl [6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]carbamate

Product 1

HCID 591342523-Amino-6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dioneYield 91.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

206 ml (1.44 mmol) of trimethylsilyl iodide (TMSI) are added to a solution of 250 mg (0.36 mmol) of benzyl [6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]carbamate in 10 ml of CH3CN at 0° C. The reaction solution is allowed to reach room temperature and is stirred at this temperature for 2 h. 5 ml of MeOH are added to the reaction solution, and then the solution is concentrated in vacuo. The residue is purified on a 5 g SCX cartridge (eluted with MeOH followed by 3N NH3/MeOH). 185 mg of the desired compound are obtained as a white powder. LC/MS 558.07 (calculated, monoisotopic); measured value (M+H)+: 559.10

Workup

  1. customto reach room temperature
  2. concentrationthe solution is concentrated in vacuo
  3. customThe residue is purified on a 5 g SCX cartridge (eluted with MeOH followed by 3N NH3/MeOH)

Sources & evidence

ORD record
ord-a7c345ef009348a783e94dbc9585f010
Source dataset
uspto-grants-2011_08
Patent number
US07994168B2

Reaction notes

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